The aromatic mercaptans are a known class of compounds having many members. Various members of the group have heretofore been converted to the corresponding aryl chloromethyl sulfides by various procedures. German Patent 845,511 describes the preparation of aryl chloromethyl sulfides by treating 1 mole of an aromatic mercaptan with at least 1 mole of formaldehyde in the presence of hydrogen chloride. Dolman et al., Rec. Trav. Chim., 88, 417(1969), describe the reaction of 1 mole of an aromatic mercaptan with 1 mole of formaldehyde in the presence of a catalytic amount of sodium methoxide to give the corresponding aryl hydroxymethyl sulfide which is subsequently reacted with 1.1 mole of thionyl chloride to afford the corresponding aryl chloromethyl sulfide. Senning and Lawesson, Acta Chem. Scand., 16, 117(1962), describe the preparation of pentachlorophenyl chloromethyl sulfide by the chlorination of pentachlorophenyl methyl sulfide with chlorine in refluxing carbon tetrachloride.
The aryl chloromethyl sulfides are useful as pesticides. The aryl chloromethyl sulfides are also excellent alkylating agents due to the lability of the chlorine atom in nucleophilic displacements. For example, the aryl chloromethyl sulfides have been heretofore reacted with potassium thiocyanate in acetone to give the corresponding (arylthio)methyl thiocyanates which are excellent fungicides (Dolman et al., supra).